JPWO2019208797A5 - - Google Patents
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- Publication number
- JPWO2019208797A5 JPWO2019208797A5 JP2020515615A JP2020515615A JPWO2019208797A5 JP WO2019208797 A5 JPWO2019208797 A5 JP WO2019208797A5 JP 2020515615 A JP2020515615 A JP 2020515615A JP 2020515615 A JP2020515615 A JP 2020515615A JP WO2019208797 A5 JPWO2019208797 A5 JP WO2019208797A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- azetidin
- carboxylic acid
- hydroxy
- acetyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 161
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 125
- 150000001875 compounds Chemical class 0.000 claims 81
- 150000003839 salts Chemical class 0.000 claims 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 54
- -1 pyrrolidin-2-ylcarbonylamino group Chemical group 0.000 claims 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 27
- 125000002723 alicyclic group Chemical group 0.000 claims 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 12
- 239000005711 Benzoic acid Substances 0.000 claims 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 10
- 235000010233 benzoic acid Nutrition 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 239000005973 Carvone Substances 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 7
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 229960004889 salicylic acid Drugs 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims 1
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims 1
- CYBUGJGACUUUDY-UHFFFAOYSA-N 2-hydroxy-7-[1-(1H-1,2,4-triazole-5-carbonyl)azetidin-3-yl]oxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid Chemical compound OB1OC2=C(CC1)C=CC(=C2C(=O)O)OC1CN(C1)C(=O)C1=NNC=N1 CYBUGJGACUUUDY-UHFFFAOYSA-N 0.000 claims 1
- XHJXMFBVADDJEB-UHFFFAOYSA-N 2-hydroxy-7-[1-[2-(4-nitrotriazol-1-yl)acetyl]azetidin-3-yl]oxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid Chemical compound OB1OC2=C(CC1)C=CC(=C2C(=O)O)OC1CN(C1)C(CN1N=NC(=C1)[N+](=O)[O-])=O XHJXMFBVADDJEB-UHFFFAOYSA-N 0.000 claims 1
- UAQQZIGHHORKCP-UHFFFAOYSA-N 2-hydroxy-7-[1-[2-[4-(hydroxymethyl)triazol-1-yl]acetyl]azetidin-3-yl]oxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid Chemical compound OB1OC2=C(CC1)C=CC(=C2C(=O)O)OC1CN(C1)C(CN1N=NC(=C1)CO)=O UAQQZIGHHORKCP-UHFFFAOYSA-N 0.000 claims 1
- HZQRFFFVVIWGFS-UHFFFAOYSA-N 2-hydroxy-7-[1-[2-[5-(hydroxymethyl)triazol-1-yl]acetyl]azetidin-3-yl]oxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid Chemical compound OB1OC2=C(CC1)C=CC(=C2C(=O)O)OC1CN(C1)C(CN1N=NC=C1CO)=O HZQRFFFVVIWGFS-UHFFFAOYSA-N 0.000 claims 1
- ZIHXVQRGBQHVJI-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-(1-methylsulfonylazetidin-3-yl)oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)S(=O)(=O)C)O ZIHXVQRGBQHVJI-UHFFFAOYSA-N 0.000 claims 1
- YNCXOZLNIAUZRR-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-(1-pyridin-3-ylsulfonylazetidin-3-yl)oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)S(=O)(=O)C=1C=NC=CC=1)O YNCXOZLNIAUZRR-UHFFFAOYSA-N 0.000 claims 1
- OYCAMXSOVOSKFZ-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1-oxidopyridin-1-ium-2-yl)sulfonylazetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)S(=O)(=O)C1=N(C=CC=C1)=O)O OYCAMXSOVOSKFZ-UHFFFAOYSA-N 0.000 claims 1
- HHKMAXXAFPFBBL-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1H-1,2,4-triazol-5-ylsulfonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)S(=O)(=O)C1=NN=CN1)O HHKMAXXAFPFBBL-UHFFFAOYSA-N 0.000 claims 1
- IBTXYJQXMBRMHC-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1H-1,2,4-triazole-5-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1=NNC=N1)O IBTXYJQXMBRMHC-UHFFFAOYSA-N 0.000 claims 1
- YNKLBKKYSNZXQC-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1H-imidazol-5-ylsulfonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)S(=O)(=O)C=1N=CNC=1)O YNKLBKKYSNZXQC-UHFFFAOYSA-N 0.000 claims 1
- TZOHLOJSVSBWEP-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C=1NC=CN=1)O TZOHLOJSVSBWEP-UHFFFAOYSA-N 0.000 claims 1
- RYNRGHVAHAVJAK-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(1H-imidazole-5-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C=1N=CNC=1)O RYNRGHVAHAVJAK-UHFFFAOYSA-N 0.000 claims 1
- UHCJUSGUCAYOAL-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-imidazol-1-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CN1C=NC=C1)=O)O UHCJUSGUCAYOAL-UHFFFAOYSA-N 0.000 claims 1
- JLAYCHYYLORDTQ-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-methylsulfanylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CSC)=O)O JLAYCHYYLORDTQ-UHFFFAOYSA-N 0.000 claims 1
- PKSUCUHJUGTKOI-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-morpholin-2-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1CNCCO1)=O)O PKSUCUHJUGTKOI-UHFFFAOYSA-N 0.000 claims 1
- JQWGUUUODPAHSM-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-phenylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1=CC=CC=C1)=O)O JQWGUUUODPAHSM-UHFFFAOYSA-N 0.000 claims 1
- LGBGBFWSGVHXJR-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-piperazin-2-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1NCCNC1)=O)O LGBGBFWSGVHXJR-UHFFFAOYSA-N 0.000 claims 1
- NBPKEQHNTPKWAD-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-piperidin-2-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1NCCCC1)=O)O NBPKEQHNTPKWAD-UHFFFAOYSA-N 0.000 claims 1
- NCSYWEQIRPGYSA-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-piperidin-3-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1CNCCC1)=O)O NCSYWEQIRPGYSA-UHFFFAOYSA-N 0.000 claims 1
- MHDSERQAXQBIQN-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-piperidin-4-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1CCNCC1)=O)O MHDSERQAXQBIQN-UHFFFAOYSA-N 0.000 claims 1
- VTCOOYVQTDJWBG-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-pyridin-2-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1=NC=CC=C1)=O)O VTCOOYVQTDJWBG-UHFFFAOYSA-N 0.000 claims 1
- OMGPSSPYEGGISC-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-pyridin-3-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC=1C=NC=CC=1)=O)O OMGPSSPYEGGISC-UHFFFAOYSA-N 0.000 claims 1
- BMRUUVAUDJNSKX-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-pyridin-4-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1=CC=NC=C1)=O)O BMRUUVAUDJNSKX-UHFFFAOYSA-N 0.000 claims 1
- YPTATZAQFRAWLH-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-pyrrolidin-2-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1NCCC1)=O)O YPTATZAQFRAWLH-UHFFFAOYSA-N 0.000 claims 1
- KGZQCIIBASIJAS-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(2-pyrrolidin-3-ylacetyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1CNCC1)=O)O KGZQCIIBASIJAS-UHFFFAOYSA-N 0.000 claims 1
- MCUPJIGUPKMKMO-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(3-phenylpropanoyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CCC1=CC=CC=C1)=O)O MCUPJIGUPKMKMO-UHFFFAOYSA-N 0.000 claims 1
- XDSOIZILCWLDGP-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(3-pyrrolidin-2-ylpropanoyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CCC1NCCC1)=O)O XDSOIZILCWLDGP-UHFFFAOYSA-N 0.000 claims 1
- ASVFBFBJGJGJHF-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(6-methyl-4-oxo-1H-pyridine-3-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C=1C=NC(=CC=1O)C)O ASVFBFBJGJGJHF-UHFFFAOYSA-N 0.000 claims 1
- QSBRWBREBJGWIL-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(hydroxycarbamoyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(NO)=O)O QSBRWBREBJGWIL-UHFFFAOYSA-N 0.000 claims 1
- KXGOQHZGLFUCBW-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(piperidine-2-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1NCCCC1)O KXGOQHZGLFUCBW-UHFFFAOYSA-N 0.000 claims 1
- VXWXZEGSDASMQJ-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(piperidine-3-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1CNCCC1)O VXWXZEGSDASMQJ-UHFFFAOYSA-N 0.000 claims 1
- YQWUBRUGRAEOBT-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(piperidine-4-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1CCNCC1)O YQWUBRUGRAEOBT-UHFFFAOYSA-N 0.000 claims 1
- KPTUIWMNFSVFGW-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(pyridine-2-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1=NC=CC=C1)O KPTUIWMNFSVFGW-UHFFFAOYSA-N 0.000 claims 1
- BWVSILHCNHOAFY-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(pyridine-3-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C=1C=NC=CC=1)O BWVSILHCNHOAFY-UHFFFAOYSA-N 0.000 claims 1
- HFWQFWBWOZHICY-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)C1CNCC1)O HFWQFWBWOZHICY-UHFFFAOYSA-N 0.000 claims 1
- XDBSEIDWCSYJSR-GFCCVEGCSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[(2R)-pyrrolidine-2-carbonyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@@H]1NCCC1)=O)O XDBSEIDWCSYJSR-GFCCVEGCSA-N 0.000 claims 1
- HPMKNISRCBTRFP-ZYHUDNBSSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[(2R,4R)-4-(trifluoromethyl)pyrrolidine-2-carbonyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@@H]1NC[C@@H](C1)C(F)(F)F)=O)O HPMKNISRCBTRFP-ZYHUDNBSSA-N 0.000 claims 1
- FEVVGDPEDZWOGY-KFJBMODSSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[(2S)-4-hydroxypyrrolidine-2-carbonyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C([C@H]1NCC(C1)O)=O)O FEVVGDPEDZWOGY-KFJBMODSSA-N 0.000 claims 1
- IPNBQFYLKYTUCB-ZDUSSCGKSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(=O)[C@H]1OCCC1)O IPNBQFYLKYTUCB-ZDUSSCGKSA-N 0.000 claims 1
- LCJJPWHCQXKNPD-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(1,2,4-triazol-1-yl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CN1N=CN=C1)=O)O LCJJPWHCQXKNPD-UHFFFAOYSA-N 0.000 claims 1
- ICAKKUIELJYNED-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(1H-imidazol-5-yl)-2-(methylamino)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(C(NC)C=1N=CNC=1)=O)O ICAKKUIELJYNED-UHFFFAOYSA-N 0.000 claims 1
- GNEZLVGPWSKRMU-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(1H-imidazol-5-yl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1=CN=CN1)=O)O GNEZLVGPWSKRMU-UHFFFAOYSA-N 0.000 claims 1
- XASRWOFGNJTFGG-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(2H-tetrazol-5-yl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC=1N=NNN=1)=O)O XASRWOFGNJTFGG-UHFFFAOYSA-N 0.000 claims 1
- HBLURODPWPXCOD-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(2H-triazol-4-yl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC=1N=NNC=1)=O)O HBLURODPWPXCOD-UHFFFAOYSA-N 0.000 claims 1
- LWAIWDGZZCZPAJ-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1NCCNC1=O)=O)O LWAIWDGZZCZPAJ-UHFFFAOYSA-N 0.000 claims 1
- XVUWIGASKLRTLK-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(4-hydroxyphenyl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CC1=CC=C(C=C1)O)=O)O XVUWIGASKLRTLK-UHFFFAOYSA-N 0.000 claims 1
- DBFMQHDYCDEITN-UHFFFAOYSA-N 3-(2-boronoethyl)-2-hydroxy-6-[1-[2-(4-nitrotriazol-1-yl)acetyl]azetidin-3-yl]oxybenzoic acid Chemical compound B(O)(O)CCC=1C(=C(C(=O)O)C(=CC=1)OC1CN(C1)C(CN1N=NC(=C1)[N+](=O)[O-])=O)O DBFMQHDYCDEITN-UHFFFAOYSA-N 0.000 claims 1
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| JP2023156567A JP7598594B2 (ja) | 2018-04-27 | 2023-09-21 | オキソ置換化合物 |
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| JP2018087761 | 2018-04-27 | ||
| JP2018087761 | 2018-04-27 | ||
| PCT/JP2019/018011 WO2019208797A1 (ja) | 2018-04-27 | 2019-04-26 | オキソ置換化合物 |
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| EP4049680A4 (en) * | 2019-10-25 | 2024-01-10 | Sumitomo Pharma Co., Ltd. | NEW SUBSTITUTED CONDENSED RING CONNECTION |
| US11476003B2 (en) * | 2020-12-15 | 2022-10-18 | Biodesix, Inc. | Method for predicting risk of unfavorable outcomes, e.g., in COVID-19 hospitalization, from clinical characteristics and basic laboratory findings |
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| MX2015008627A (es) | 2013-01-04 | 2015-09-23 | Rempex Pharmaceuticals Inc | Derivados de acido boronico y usos terapeuticos de los mismos. |
| KR20150103269A (ko) | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
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| WO2016003929A1 (en) | 2014-07-01 | 2016-01-07 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
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